Water → HCID 15616687, compound

HRID 1193625Notes

Reaction equation

HRID 1193625 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][CH:8]=2)[C:5]([S:15][CH:16]([CH3:18])[CH3:17])=[N:4][C:3]=1[C:19](=[O:23])[C:20]([CH3:22])=[CH2:21].I([O-])(=O)(=O)=[O:25].[Na+].O>CO>[Cl:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH3:14])=[CH:11][CH:12]=2)[C:5]([S:15]([CH:16]([CH3:17])[CH3:18])=[O:25])=[N:4][C:3]=1[C:19](=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

5

Reactant 3

HCID 962WaterHCID 19989905HCID 19989905, compoundHCID 23667635Sodium periodate

Product 1

HCID 15616687HCID 15616687, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.0 g (8.6 mmol) of [5-chloro-1-(4-ethylphenyl)-2-(prop-2-ylthio)-imidazol-4-yl]-2-methyl-2-propen-1-one and 2.3 g (11 mmol) of sodium metaperiodate was heated at 50° C. for 3 hours in 30 ml of 90% aqueous methanol. The mixture was cooled and poured into water. Extraction with dichloromethane yielded an oil which was purified by flash chromatography on silica (20% ethyl acetate in petroleum ether) to obtain 1.3 g (41%) of [5-chloro-1-(4-ethylphenyl)-2-(prop-2-ylsulfinyl)-imidazol-4-yl]-2-methyl-2-propen-1-one as cream-colored crystals melting at 83°-4° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionExtraction with dichloromethane
  3. customyielded an oil which
  4. customwas purified by flash chromatography on silica (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a4f86bd6b3a24d18bc77b7ba9a4c71b2
Source dataset
uspto-grants-1989_03
Patent number
US04810828

Reaction notes

Loading…